diff --git a/src/wp-includes/js/tinymce/plugins/wpeditimage/plugin.js b/src/wp-includes/js/tinymce/plugins/wpeditimage/plugin.js
index 0366c28544..4a81ca9ef8 100644
--- a/src/wp-includes/js/tinymce/plugins/wpeditimage/plugin.js
+++ b/src/wp-includes/js/tinymce/plugins/wpeditimage/plugin.js
@@ -963,22 +963,28 @@ tinymce.PluginManager.add( 'wpeditimage', function( editor ) {
 
 			if ( node.nodeName === 'IMG' ) {
 				wrap = editor.dom.getParent( node, '.mceTemp' );
+
+				if ( ! wrap && node.parentNode.nodeName === 'A' && ! hasTextContent( node.parentNode ) ) {
+					wrap = node.parentNode;
+				}
 			}
 		} );
 
 		editor.on( 'drop', function( event ) {
-			var rng;
+			var dom = editor.dom,
+				rng = tinymce.dom.RangeUtils.getCaretRangeFromPoint( event.clientX, event.clientY, editor.getDoc() );
 
-			if ( wrap && ( rng = tinymce.dom.RangeUtils.getCaretRangeFromPoint( event.clientX, event.clientY, editor.getDoc() ) ) ) {
+			// Don't allow anything to be dropped in a captioned image.
+			if ( dom.getParent( rng.startContainer, '.mceTemp' ) ) {
+				event.preventDefault();
+			} else if ( wrap ) {
 				event.preventDefault();
 
-				if ( ! editor.dom.getParent( rng.startContainer, '.mceTemp' ) ) {
-					editor.undoManager.transact( function() {
-						editor.selection.setRng( rng );
-						editor.selection.setNode( wrap );
-						editor.dom.remove( wrap );
-					} );
-				}
+				editor.undoManager.transact( function() {
+					editor.selection.setRng( rng );
+					editor.selection.setNode( wrap );
+					dom.remove( wrap );
+				} );
 			}
 
 			wrap = null;